a) The structure of penicillin G is shown below. Circle the most acidic proton in the structure and give an approximate pKą value for that proton in the box povided. Penicillin G + NH3 Penicillin G H orty b) Based on your answer to part (a), calculate the equilibrium constant for the reaction of penicillin G with ammonia. Be sure to show your work for partial credit! Penicillin G pK₂ = Approximate pK₂ = SH NH4 Keq = 1 OH c) The pką value of protonated penicillin G is approximately 6. Based on this information, calculate the RK value ofthe thiol shown below, given that the equilibrium constant for the reaction is approximately O₂N + Deprotonated Penicillin G Kea = + Protonated Penicillin G pK₂ = 6

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter9: Addition Via Cyclic Intermediate
Section: Chapter Questions
Problem 2E
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6..
a) The structure of penicillin G is shown below. Circle the most acidic proton in the structure and give an
approximate pKa value for that proton in the box povided.
ortx
Penicillin G +
b) Based on your answer to part (a), calculate the equilibrium constant for the reaction of penicillin
G with ammonia. Be sure to show your work for partial credit!
NH3
Penicillin G
Penicillin G
O₂N
Approximate pka =
0
pka =
SH
NH4
Keq
c) The pka value of protonated penicillin G is approximately 6. Based on this information, calculate the
pKa value ofthe thiol shown below, given that the equilibrium constant for the reaction is approximately 1.
OH
= 1
O₂N
+
Deprotonated
Penicillin G
Kea
=
Protonated
Penicillin G
pK₂ = 6
Transcribed Image Text:6.. a) The structure of penicillin G is shown below. Circle the most acidic proton in the structure and give an approximate pKa value for that proton in the box povided. ortx Penicillin G + b) Based on your answer to part (a), calculate the equilibrium constant for the reaction of penicillin G with ammonia. Be sure to show your work for partial credit! NH3 Penicillin G Penicillin G O₂N Approximate pka = 0 pka = SH NH4 Keq c) The pka value of protonated penicillin G is approximately 6. Based on this information, calculate the pKa value ofthe thiol shown below, given that the equilibrium constant for the reaction is approximately 1. OH = 1 O₂N + Deprotonated Penicillin G Kea = Protonated Penicillin G pK₂ = 6
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